Working notes
I did not come from software.
Fifteen years in engineering in the UK, nearly a decade of it in the car industry, and I could not have told you what an API was. Now I run a bespoke software and automation agency out of the UK, with clients here and in the United States. This is the unglamorous record of what happened in between — plus straight answers to the questions businesses actually ask me about AI, taken from the calls where they asked them.
78 shown · 32 journey · 46 questions answered
2026
Can the software do the quote and a human just check it?
An engineering owner asked me this last week, almost word for word. The answer is yes, and the reason it works has very little to do with the AI.
The work I would not hand over to software
Somebody asked me where all this ends. Here is the line I draw, and the test I use to decide which side of it a job sits on.
Nobody here will connect their inbox to an AI
A publisher said something to me last week that explains more failed AI projects than any report I have read. He knows owners who would not connect their inbox to one of these tools whatever it did for them, and the reason was not the technology.
The build was finished. Then nobody logged in for twenty days.
We got the whole team onto a call and watched them log in. It went well. Then the thing sat untouched for nearly three weeks.
Sixty hours of paperwork is not a paperwork problem
A sales manager told me the application in front of him would take sixty hours. Then he said the thing I have repeated to three people since.
Can you make it talk to the system we already use?
This question decides whether a project is straightforward or a nightmare, and it nearly always gets asked last. Two companies asked me it this month and I couldn't answer either of them.
I was told to log every hour for a month, so I did
Someone asked me where my time goes and I could not answer it with anything other than a feeling. His prescription was to log everything for thirty days, business and personal. The only reason I agreed is that I am not the one doing the logging.
Nothing is broken. Why would we spend money on it?
A director asked me this about an online shop that has been working quietly for four years. It is the most reasonable objection there is, and the answer has almost nothing to do with features.
Why "nearly finished" can last for months
One question came up on my calls more than any other this summer, and it was a small one: is it finished yet? Here is what I changed so the answer arrives sooner.
What owners really mean when they ask for a new website
Websites have come up on most of my calls lately. The request usually starts with how the site looks. The conversation that follows rarely stays there.
Your old records are the part that catches owners out
When owners picture a new system, they picture what they'll see on screen. The years of records sitting in the old one are what most often catch them out.
Record yourself doing the job, with the sound on
The most useful thing a client sent me this month was a screen recording of somebody doing a dull, repetitive task. It changed what I proposed, and it cost her about ten minutes.
When head office has to sign it off, start here
If you run the UK arm of a bigger group, the decision about new software often isn't yours. Here is what I would do before anyone writes a proposal.
Why I only take on two or three new clients a month
My old plan for growth was more clients, more hours and more of me. I've capped it instead, and this is the arithmetic that changed my mind.
I rebuilt my own website in a weekend, without a developer
The old one was made with an AI site builder. The new one is plain files I own. Both choices were right, at different times.
What I would tell myself at the start
A short list for the version of me who had just decided to do this and had no idea what he was walking into.
What clients ask for versus what they need
Four requests I hear constantly, and what the person is usually describing underneath.
I automated my own agency before selling anyone else automation
It started as hypocrisy avoidance. It became my best sales asset.
The one-page blueprint that replaced my proposals
My proposals ran past twenty pages. Nobody read past four.
Everyone is selling AI right now. How do we tell who is any good?
Six questions that separate people who have delivered from people who have read about it.
Do you work with clients outside the UK?
Yes — and here is what genuinely differs, plus the practical things that bite.
What I look for in a developer now
It is not the technical test. It is what happens when I describe something badly.
How do you test it before it goes anywhere near our customers?
Including the test that matters most, which is not a technical one.
The build that worked perfectly and only one person used
Everything shipped. Everything worked. Adoption was one person. The most useful failure I have had.
Why is the first phase so small?
Clients sometimes want to go faster and bigger. Here is why I hold the line.
How do you stop us buying something we do not need?
A client asked me this directly, which was a good sign about them and a hard question about me.
The three questions I ask in every first meeting
They have not changed in two years and they have never once failed to find the real problem.
Will you sign an NDA?
Yes, without drama. Here is what I will and will not agree to, and why.
A year of saying no to features
I kept a tally of every feature I talked a client out of. The number surprised me.
The month the work dried up
Two deals moved, one client paused, and I learned what my pipeline actually was.
Does it need internet? Our people work in places with no signal.
A question from the real world that a lot of software ignores, at its cost.
Are we too small — or too big — for you?
The number that matters is not headcount or turnover.
How do you decide what to automate first?
Four questions on the back of an envelope, and the trap that catches almost everyone.
Can you work alongside our own developers?
Yes, and it is often the best arrangement — provided one thing is settled up front.
What if the person who championed this leaves?
One of the most common ways good software quietly dies, and it is preventable.
Who trains our team, and what if they hate it?
Adoption is the whole game, and it is decided long before the training session.
What exactly do we get at the end?
A checklist you can hold any supplier to, including me.
The client I turned down, and what it taught me
The money was good and the project was interesting. Everything else was wrong, and I nearly ignored it.
Do you work fixed price or day rate?
Fixed price per phase, and the reason is about who carries which risk.
We know something is wrong but we do not know what to ask for
This is the healthiest possible starting position, and I would rather have it than a detailed spec.
Is our data used to train the AI?
The single most common worry, and the answer is more reassuring than most people expect — with one condition.
My first client in the United States
Everything I had been warned about was wrong, and the thing nobody mentioned nearly sank it.
What happens when we change our minds mid-build?
You will, and that is normal. What matters is that it is visible rather than absorbed in silence.
What if we want to bring it in-house later?
Good. That should be possible on any Tuesday, without a negotiation.
Do you host it, or do we?
You do, in an account with your name on it, and I will explain exactly why I insist on that.
The week I went all in
Doing this alongside something else had a ceiling, and I hit it. What actually changed was not the hours.
Can you take over something another developer built?
Yes, and it is more common than anyone admits. Here is what I look at before saying yes.
What is the difference between automation and AI?
It matters commercially, because one of them is much cheaper and more reliable than the other.
How will we know whether it actually worked?
Agree the measure before the build, because afterwards everyone remembers the baseline differently.
What is discovery, and why am I paying for it?
A fair challenge: you have not built anything yet. Here is exactly what you get and why it is not a sales document.
2025
Do you need to understand our industry?
Less than you would think, and the reason why is the useful part.
The year I stopped apologising for not being technical
I opened every meeting undermining myself. It was costing me work and it was not even accurate.
We already have an IT company. Where do you fit?
Usually alongside them, not instead of them — and getting this wrong makes your life much harder.
How to work with developers when you cannot code
You do not need to read their code. You need to tell whether what they built matches what the client meant.
Which AI do you actually use, and does it matter?
Asked often, usually as a proxy for "do you know what you are doing". Here is a straight answer.
Why I stopped saying "AI" in sales calls
The word does two jobs at once and you do not get to choose which one it does in the other person.
Can we start small and see how it goes?
Yes. In fact I will usually push you towards it even when you are ready to spend more.
How much of my team's time will this take?
Underestimated by nearly every supplier, including me, early on. Here are the real numbers.
The quote that nearly broke me
I underpriced a build so badly that finishing it properly cost me money. What I learned was not about numbers.
What does it cost to keep running once it is built?
The question that should be asked before you sign and usually is not. One client admitted he never had that conversation, and it cost him.
Will it work with the systems we already have?
"Will the AI integrate into existing software, or will you create a separate application?" The answer decides whether anyone uses it.
The best question I ever stole from a client
Eight words that turn a vague automation conversation into a decision.
Why not just use ChatGPT ourselves?
Sometimes you should, and I will tell you when. Here is where it stops working.
How does GDPR work when there is AI involved?
Asked on more calls than any other compliance question. Not legal advice — just what I have actually had to get right.
I started charging for discovery, and the work got better
Free scoping produced polite meetings and vague proposals. Charging changed the work, the access, and the answer.
You are a small outfit. What happens when you are on holiday?
Asked directly, and it deserved a better answer than the one I gave at the time.
How long does this take, from first call to something we can use?
"We gave it a go-ahead to discovery and write some software — how long does that take?" A straight answer, including the bit that is your side, not mine.
The first thing I got badly wrong: I built exactly what they asked for
A client asked for eleven features. I delivered eleven features. Two got used, and that was my fault, not theirs.
Who owns the code, the data and the report?
"Why don't I own the report?" was asked of someone else, in front of me, and it changed how I write contracts.
What a coaching qualification taught me about scoping software
Scoping and coaching are the same job in different clothes: getting the real problem out of someone who has stopped noticing it.
What happens when the AI gets it wrong?
"Did this hallucinate or what?" It will, sometimes. The question is what you built around it.
Nobody wants AI. They want Thursday afternoon back.
Every enquiry that opens with "we need an AI strategy" is a person describing a Thursday they never get back.
Will this replace my team?
Rarely asked out loud by the person paying. Always present in the room. Here is how I handle it.
Off-the-shelf or custom: how do you actually decide?
"Why are we spending so much money on software when we could have something off the shelf for a few hundred quid a month?" A completely reasonable question with a real answer.
The first thing anyone paid me to build
It was small, it was unglamorous, and I have never been more frightened of an invoice.
Where is our data stored, and who can see it?
A prospect asked me this twice in one meeting, which told me I had not answered it properly the first time. Here is the answer I give now.
What does bespoke software actually cost?
The honest answer to the question everyone wants answered on the first call, including why I will not give you a number in the first ten minutes.
I was a life coach who could not read a line of code
The most technical thing I did in a week was reschedule a Zoom. This is where it started.